Beta-halogen-ethylaminobenzoic esters and their derivatives



ill

am. We a am it JEAN" .dLIll'illTfil Gl-ti AWE) JII'UANNY LATNZHWIVUN, Ftron, lFlldANGld, AFaiEzIG-llltilltd Tittdiltlliltilllllil CI-IIIWCIQUIEDEfl 'llgliltliifl :DU Ell-TUNE (ANCTTENNEMENT GIJLLIATW), l". MUNN'ETET CAYJR nine), or rears; rnan'cn.

ilfid il fiaill,

Ito Drawing.

To all whom it may concern Be it known that We, Juan hrn wneo 'ot 227Avenue de Sane, Lyon, France, a citizen of the Confederation ofSwitzerland,-

and JOANNY LANonrvoN, of 22 Rue delAnnonciade, Lyon, France, a "citizenof the Republic of France, have invented a certain new and usefulBetaHalogen-Ethylamino- 'benzoic Esters and Other Derivatives, of

which the following is a specification...

This invention has for its object the manufacture of theS-halogen-ethylaminobenzoic esters having for general formula acnpnnnoinooon.

where B represents an alkyl radical and a halogen.

According to this invention the ti-halogenethyl -aininobenzoic esterscan be ob tained by treating t-oxyethylaniinobenzoic esters having thegeneral formula OHCI-T CTTJJHG TLGUGhlt.

With haiogenating reagents such as phos' phorus or sulfur halides,thionyl chlorid or broinid or the like. The new esters are stableproducts and can be distilled under reduced pressure Withoutdecomposition.

Example 1. it solution of parts oi ethyl a cnyethylparaniino beneoatehaving! the iorniuia I and melting at 63 C, in parts oi benzene treetrom'moisture is poured into a mixture of parts oi phosphoruspentachlorid and of parts of benzene free from moisture. The reaction iscompleted by heating on the Water bath. The benzene and the phosphorusonychlorid are eliminated by evaporation and the residue is purified bydistillation under reduced pressure. In this manner, ethyl (tchlorethytpararninobenaoate having for formula ftpecifioatlon of LettersI'atcnt. Pa-fiqaymtgfl I i liar, 2H3, 92m, Application filed tune it,lulu. serial No. roasts.

reiacn nnoatcoo.car,

proportion of diinethylanilin, and an equal molecular proportion ofthionyl chlorid is run into the solution While cooling. The mixture isheated for a While on the Water bath and then treated with lukewarmWater. The dimethylanilin hydrochlorid di solves while the ethyl(tchlorethylparamino-,benzoate separates in granules. The product ispurified by Washing "with Water and by distilling" under reducedpressure. The yields are approximately in agreement with theory.

The products forming the subject 'rnatter of this invention are usefulas local anesthetics, and as raw material. for preparing otherpharmaceutical products.

it is understood that the above examples are given by way ofillustrative examples only, and may be varied in details accord-- ing tothe particular reagents employed What we desire to claim and secure byLetters Patent is The new industrial products, the {ihalegen-ethylaminobenzoic esters which may be obtained by the abovedescribed. process being stable products which can be distilled underreduced pressure Without decomposition. y

In Witness Whereoi We have hereunto signed our names in the presence oftwo subscribing WlbllQSSt-ES.

